The 1996 film had a star-studded cast including Natalie Portman, Uma Thurman, Rosie O'Donnell and more

By Drew Mackie
Updated February 09, 2016 12:45 PM
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Twenty years ago this week – Feb. 9, 1996 – the romcom-dramedy Beautiful Girls first opened in theaters. The film centers around Willie (Timothy Hutton), who returns home for his high school reunion in a small Massachusetts town. It’s funny, it’s heartwarming, and it features one of the better ensemble casts of the 1990s.

In honor of the film’s 20th anniversary, we’re pulling out the yearbook and looking up the film’s cast to what they’ve been up to over the past 20 years.

Timothy Hutton

Hutton won Best Supporting Actor in 1981 for Ordinary People when he was only 20. To this day he’s the youngest-ever male actor to win an Oscar. Since Beautiful Girls, Hutton has starred in Kinsey (2004), The Good Shepherd (2006), on four seasons of Leverage (2008-2012), and starting in 2015 on American Crime, for which he picked up an Emmy nomination.

Hutton, who split from Debra Winger in 1990, married Aurore Giscard d’Estaing – an illustrator and the niece of the former French president Val ry Giscard d’Estaing – in 2001. They have a son, Milo (born 2001), but separated in 2009.

Matt Dillon

Playing Tommy “Birdman” Rowland, the former school jock who never made good on his potential, Dillon bounced from Beautiful Girls into a string of ’90s hits: In & Out (1997), There’s Something About Mary and Wild Things (both 1998). Most recently, Dillon starred in the surprise hit miniseries Wayward Pines, which was picked up for a second season that will air later this year. Dillon dated his Mary costar Cameron Diaz from 1995 to 1998.

Natalie Portman

Arguably the most successful actor in the entire cast, Portman was only 15 when she played the girl next door who nurses an innocent crush on Hutton’s character. Portman went on to bigger things (the Star Wars prequels) as well as Garden State (2004), Closer (2004), V for Vendetta (2006) and most notably Black Swan (2010), which ended up getting her a Best Actress Oscar, a husband (in the form of costar Benjamin Millepied) and a son (Aleph, born in 2011). She’s next playing Jacqueline Kennedy in Jackie, a biopic due in 2017.

Lauren Holly

Holly was still attached to her Dumb and Dumber costar Jim Carrey at the time Beautiful Girls came out. They’d split in 1997, and Holly would go on to star in films such as Any Given Sunday (1999), What Women Want (2000), as well as three seasons of NCIS (2005-2008). She’s been on the Canadian procedural Motive since 2013. Holly married investment banker Francisco Greco in 2001, and together they have three children.

Rosie O’Donnell

Though O’Donnell would continue to act in films after Beautiful Girls – among them, Harriet the Spy (1996) and Tarzan (1999) – her career would soon move toward smaller screens. The Rosie O’Donnell show premiered in 1996 and lasted for more than 1,000 episodes. She still acts occasionally, but she’s probably best known today for being an on-air personality as a result of joining The View in 2006 and again in 2014.

O’Donnell famously came out in 2002, after playing a lesbian mom on an episode of Will & Grace. She married Kelli Carpenter in 2004, and the couple had three children before splitting in 2007. O’Donnell then married Michelle Rounds in 2012, and the couple adopted a daughter before divorcing in 2014. In 2015, O’Donnell’s home life made news when her oldest daughter, Chelsea, went missing. She was later found living with her boyfriend. O’Donnell and her daughter remain estranged. In October, O’Donnell split from actress Tatum O’Neal.

Rosie O’Donnell Responds to Question About Daughter’s Disappearance: ‘No Mom Is Perfect’

Mira Sorvino

Hutton and Portman aren’t the only ones in the cast with an Oscar. Sorvino, who played Dillon’s character’s girlfriend, had won a Best Supporting Actress award for her role in 1995’s Mighty Aphrodite. Since 1996, Sorvino’s biggest film hit was 1997’s Romy and Michele’s High School Reunion, but she’s been acting ever since. Most recently, she’s appeared on the series Psych, Falling Skies and Stalker.

In 2005, Sorvino married actor Christopher Backus, and the couple has four children together – Mattea, Johnny, Holden and Lucia.

Uma Thurman

Beautiful Girls

was Thurman’s first major picture after Pulp Fiction, for which she was nominated for Best Supporting Actress. Since then, she starred in The Truth About Cats and Dogs (1996), Batman & Robin (1997) and Gattaca (also 1997). She re-teamed with Quentin Tarantino in 2003 for Kill Bill, and in 2017 she’ll team up with another Tarantino regular, Tim Roth, in The Brits Are Coming.

Thurman married her Gattaca costar Ethan Hawke in 1998, and the couple had two children, Maya Ray and Levon, before splitting in 2003. In 2012, she had a daughter, Rosalind Arusha Arkadina Altalune Florence Thurman-Busson, with French financier Arpad Busson. Thurman and Busson have been engaged twice – in 2009 and 2014.

Martha Plimpton

The Goonies costar was all grown up by 1996. She’s continued to act in movies, appearing in indie flicks such as Pecker (1998) and 200 Cigarettes (1999), but she’s really found her home on TV, starring on four seasons of the sitcom Raising Hope and in a recurring role on The Good Wife that won her an Emmy in 2012. Her new sitcom, The Real O’Neals debuts in March on ABC. Plimpton also sings, and in 2010 performed a one-woman show, Martha Plimpton Sings? at Lincoln Center.

Michael Rapaport

Before Beautiful Girls, Rapaport was a character actor specializing in comedy roles. After Beautiful Girls, he’s still that, but now he has a lengthy resume under his belt. Among Rapaport’s most notable roles are Deep Blue Sea (1999), Bamboozled (2000), Hitch (2005) and The Heat (2013). He played Phoebe’s police officer boyfriend on Friends, and he also starred in three seasons of Boston Public, two of The War at Home and had a recurring role on My Name Is Earl.

Annabeth Gish

Gish played Tracy, the longterm girlfriend of Hutton’s character. Since, her most notable role is probably as Agent Reyes, who joined the cast of The X-Files later in the show’s run. (And she’s reprising the role later this month!) However, Gish also starred in Double Jeopardy (1999) and The Celestine Prophecy (2006), and well as on the TV shows Brotherhood, Pretty Little Liars and The Bridge.

In 2003 Gish married Wade Allen, a stuntman she met on the set of The X-Files. They have two children, Cash Alexander (born 2007) and Enzo Edward (born 2008).